Category: indole-building-block

Pyrazolopyrimide library screening in glioma cells discovers highly potent antiproliferative leads that target the PI3K/mTOR pathway was written by Valero, Teresa;Baillache, Daniel J.;Fraser, Craig;Myers, Samuel H.;Unciti-Broceta, Asier. And the article was included in Bioorganic & Medicinal Chemistry in 2020.Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester This article mentions the following:

The search for novel targeted inhibitors active on glioblastoma multiforme is crucial to develop new treatments for this unmet clin. need. Herein, we report the results from a screening campaign against glioma cell lines using a proprietary library of 100 structurally-related pyrazolopyrimidines. Data anal. identified a family of compounds featuring a 2-amino-1,3-benzoxazole moiety (eCF309 to eCF334) for their antiproliferative properties in the nM range. These results were validated in patient-derived glioma cells. Available kinase inhibition profile pointed to blockade of the PI3K/mTOR pathway as being responsible for the potent activity of the hits. Combination studies demonstrated synergistic activity by inhibiting both PI3Ks and mTOR with selective inhibitors. Based on the structure activity relationships identified in this study, five new derivatives were synthesized and tested, which exhibited potent activity against glioma cells but not superior to the dual PI3K/mTOR inhibitor and lead compound of the screening eCF324. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester).

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Recommanded Product: 7-Azaindole-5-boronic Acid Pinacol Ester

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Design, synthesis, and biological evaluation of novel trifluoromethyl indoles as potent HIV-1 NNRTIs with an improved drug resistance profile was written by Jiang, Hai-Xia;Zhuang, Dao-Min;Huang, Ying;Cao, Xing-Xin;Yao, Jian-Hua;Li, Jing-Yun;Wang, Jian-Yong;Zhang, Chen;Jiang, Biao. And the article was included in Organic & Biomolecular Chemistry in 2014.HPLC of Formula: 210345-56-5 This article mentions the following:

A novel series of trifluoromethyl indole derivatives have been designed, synthesized and evaluated for anti-HIV-1 activities in MT-2 cells. The hydrophobic constant, acute toxicity, carcinogenicity and mutagenicity were predicted. Trifluoromethyl indoles (I) and (II) showed extremely promising activities against WT HIV-1 with IC₅₀ values at the low nanomolar level, similar to efavirenz, better than nevirapine, and also possessed higher potency towards the drug-resistant mutant strain Y181C than nevirapine. Preliminary SAR and docking studies of detailed binding mode provided some insights for discovery of more potent NNRTIs. In the experiment, the researchers used many compounds, for example, Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5HPLC of Formula: 210345-56-5).

Methyl 5-bromo-1H-indole-2-carboxylate (cas: 210345-56-5) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.HPLC of Formula: 210345-56-5

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Copper-Catalyzed Successive C-C bond formations on Indoles or Pyrrole: A Convergent Synthesis of Symmetric and Unsymmetric Hydroxyl Substituted N-H Carbazoles was written by Qiao, Yu;Wu, Xin-Xing;Zhao, Yupeng;Sun, Yongqing;Li, Baoguo;Chen, Shufeng. And the article was included in Advanced Synthesis & Catalysis in 2018.Computed Properties of C8H6N2O2 This article mentions the following:

A copper-catalyzed successive C-C bond formations on indoles and pyrrole approach for the direct synthesis of hydroxyl substituted N-H carbazoles is described. The current process represents an atom-economical method for the preparation of both sym. and unsym. densely substituted and hydroxyl containing N-H carbazoles from easily accessible starting materials without the need for expensive metals and harsh reaction conditions. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Computed Properties of C8H6N2O2).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Computed Properties of C8H6N2O2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Discovery of benzo[d]oxazol-2(3H)-one derivatives as a new class of TNIK inhibitors for the treatment of colorectal cancer was written by Luo, Xinling;Yang, Ruicheng;Li, Yueshan;Zhang, Liting;Yang, Shengyong;Li, Linli. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2022.Reference of 754214-56-7 This article mentions the following:

Colorectal cancer (CRC) is one of the most commonly diagnosed cancer types and Traf2- and Nck-interacting kinase (TNIK) has been thought as a potential target for CRC treatment. Herein we report the discovery and structure-activity relationship (SAR) of benzo[d]oxazol-2(3H)-one derivatives as a new class of TNIK inhibitors. The most potent compound 8g showed an IC₅₀ value of 0.050 渭M against TNIK. It effectively suppressed proliferation and migration of colorectal cancer cells. Western blot anal. indicated that 8g could inhibit aberrant transcription activation of Wnt signaling. Collectively, this study provides a potential lead compound for subsequent drug discovery targeting TNIK. In the experiment, the researchers used many compounds, for example, 7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7Reference of 754214-56-7).

7-Azaindole-5-boronic Acid Pinacol Ester (cas: 754214-56-7) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Reference of 754214-56-7

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Iodine-catalyzed C3-formylation of indoles via C-N bond cleavage of tertiary amines under aerobic conditions was written by Lu, Lin;Xiong, Qiheng;Guo, Shengmei;He, Tianqiang;Xu, Feng;Gong, Jiuhan;Zhu, Zheng;Cai, Hu. And the article was included in Tetrahedron in 2015.Category: indole-building-block This article mentions the following:

A novel route was developed for the C3-formation of indoles using iodine as the catalyst. This transformation involves the cleavage of the C-N bond of tertiary amines by the Cross-Dehydrogenative Coupling reaction (CDC), and is well tolerated by a range of 1H-indoles under aerobic conditions. Moreover, this method can be applied to gram-scale synthesis. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Category: indole-building-block).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Synthesis of water-soluble, ring-substituted squaraine dyes and their evaluation as fluorescent probes and labels was written by Tatarets, Anatoliy L.;Fedyunyayeva, Irina A.;Dyubko, Tatyana S.;Povrozin, Yevgeniy A.;Doroshenko, Andrey O.;Terpetschnig, Ewald A.;Patsenker, Leonid D.. And the article was included in Analytica Chimica Acta in 2006.Reference of 146368-07-2 This article mentions the following:

A series of ring-substituted squaraines absorbing and emitting in the red and NIR spectral region was synthesized and their spectral and photophys. properties (quantum yields, fluorescence lifetimes) and photostabilities were measured and compared to Cy5, a commonly used fluorescent label. The absorption maxima in aqueous media were between 628 and 667 nm and the emission maxima are between 642 and 685 nm. Squaraine dyes exhibit high extinction coefficients (163,000-265,000 M^-1 cm^-1) and lower quantum yields (2-7%) in aqueous buffer but high quantum yields (up to 45%) and long fluorescence lifetimes (up to 3.3 ns) in presence of BSA. Dicyanomethylene- and thio-substituted squaraines exhibit an addnl. absorption around 400 nm with extinction coefficients between 21,500 and 44,500 M^-1 cm^-1. These dyes are excitable not only with red but also with blue diode lasers or light emitting diodes. Due to the favorable spectral and photophys. properties these dyes can be used as fluorescent probes and labels for intensity- and fluorescence lifetime-based biomedical applications. In the experiment, the researchers used many compounds, for example, 1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2Reference of 146368-07-2).

1-Ethyl-2,3,3-trimethyl-3H-indol-1-ium-5-sulfonate (cas: 146368-07-2) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Reference of 146368-07-2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

蟺-Aromatic and Sulfur Nucleophilic Partners in Cationic 蟺-Cyclizations: Intramolecular Amidoalkylation and Thioamidoalkylation Cyclization via 蠅-Carbinol Lactams was written by Hucher, Nicolas;Decroix, Bernard;Daiech, Adam. And the article was included in Journal of Organic Chemistry in 2001.Quality Control of 2-(Phenylthio)isoindoline-1,3-dione This article mentions the following:

NaBH₄ reduction of imides followed by a 蟺-cyclization of the resultant N-acyliminium ions, generated in trifluoroacetic acid conditions, afforded two positional isomers, isoindolobenzothiazolinones. These ring closures proceeded via an intramol. 伪-amidoalkylation with the classical 蟺-aromatic or the atypical sulfur atom as an internal nucleophile. A ready access to the related six-membered N,S-heterocyclic compounds such as isoindolobenzothiazinones is also described. During this reaction, we have shown that a 蠅-carbinol lactam precursor led to endocyclic and exocyclic N-acyliminium ions in equilibrium via the a cyclic aza-sulfonium ion. The latter furnished the expected products in good yields. Similarly, different 蠅-carbinol lactams substituted at C-angular position afforded the corresponding isoindolobenzothiazinones bearing an angular alkyl, aralkyl, or aryl group. In the case of Me and benzyl groups, an addnl. amount of the dehydration products was isolated. These results indicate that the isomerization-蟺-cyclization takes place via the cleavage of the thioether linkage in acidic medium. In the experiment, the researchers used many compounds, for example, 2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4Quality Control of 2-(Phenylthio)isoindoline-1,3-dione).

2-(Phenylthio)isoindoline-1,3-dione (cas: 14204-27-4) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Quality Control of 2-(Phenylthio)isoindoline-1,3-dione

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Synthesis and biological evaluation of indole-based UC-112 analogs as potent and selective survivin inhibitors was written by Wang, Qinghui;Arnst, Kinsie E.;Xue, Yi;Lei, Zi-Ning;Ma, Dejian;Chen, Zhe-Sheng;Miller, Duane D.;Li, Wei. And the article was included in European Journal of Medicinal Chemistry in 2018.Safety of 6-Nitro-1H-indole This article mentions the following:

The extensive structural modification of the recently discovered selective survivin inhibitor UC-112 and the synthesis of thirty-three new analogs I [R = (5-fluoro-1H-indazol-1-yl)methyl, 7-fluoro-indol-1-ylmethyl, 2-methyl-5-methoxy-indol-1-ylmethyl, etc.] have been reported. The structure-activity relationship (SAR) study indicated that replacement of the benzyloxy moiety in UC-112 with an indole moiety was preferred to other moieties. Among these UC-112 analogs, I (R = 5-fluoro-indol-1-ylmethyl, 5-nitro-indol-1-ylmethyl, 6-chloro-indol-1-ylmethyl, 6-methoxy-indol-1-ylmethyl) showed the most potent antiproliferative activities. Interestingly, they were more potent against the P-glycoprotein overexpressing cancer cell lines compared with the parental cancer cell lines. Mechanistic studies confirmed that new analogs maintained their unique selectivity against survivin among the IAP family members. In vivo study using I (R = 5-fluoro-indol-1-ylmethyl) in a human A375 melanoma xenograft model revealed that it effectively inhibited melanoma tumor growth without observable acute toxicity. Collectively, this study strongly supports the further preclin. development of selective survivin inhibitors based on the UC-112 scaffold. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Safety of 6-Nitro-1H-indole).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Safety of 6-Nitro-1H-indole

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Cinnamoyl amide type chiral P,olefin ligands for Pd-catalyzed reactions was written by Mino, Takashi;Fujisawa, Yohei;Yoshida, Shizuki;Hirama, Mitsuru;Akiyama, Takumu;Saito, Ryo;Yoshida, Yasushi;Kasashima, Yoshio;Sakamoto, Masami. And the article was included in Organic & Biomolecular Chemistry in 2021.Electric Literature of C8H6N2O2 This article mentions the following:

Cinnamoyl amide type chiral P,olefin ligands are synthesized. Authors successfully obtained separable diastereomers of I with axial chirality and demonstrated Pd-catalyzed asym. allylic substitution reactions of indoles using compound I as a chiral ligand with high enantioselectivities (up to 98% ee). In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Electric Literature of C8H6N2O2).

6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Electric Literature of C8H6N2O2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Induction of Apoptosis in SKOV3 and DNA Binding by Cobalt(III) Polypyridyl Complexes was written by Ravi, Ch.;Vuradi, Ravi Kumar;Avudoddi, Srishailam;Ramchander, M.;Satyanarayana, S.. And the article was included in Russian Journal of Bioorganic Chemistry in 2019.Product Details of 827-01-0 This article mentions the following:

Abstract: Three new Co(III) polypyridyl complexes [Co(phen)₂CIIP]³⁺ {CIIP = 2-(5-chloro-3a,H-isoindol-3-yl)-1H-imidazo[4,5-f][1,10]phenantholine} (phen = 1,10 phenanthroline), [Co(bpy)₂CIIP]³⁺ (bpy = 2,2′-bipyridine), and [Co(dmb)₂CIIP]³⁺ (dmb = 4,4′-dimethyl-2,2′-bipyridine) were synthesized and characterized by different spectral methods. The complexes interact with DNA in an intercalation mode as confirmed by spectroscopic titration and viscosity measurements. All three complexes cleaved the pBR322 DNA in photoactivated cleavage studies and exhibited good antimicrobial activity. Anticancer activity of these Co(III) complexes was evaluated on the SKOV3 cell line. Cytotoxicity by MTT assay showed growth inhibition in dose dependent manner. Cell cycle anal. by flow cytometry data showed increase in Sub G1 population. Annexin V FITC/PI staining confirmed that these complexes caused cell death by the induction of apoptosis. In the experiment, the researchers used many compounds, for example, 5-Chloroindole-3-carboxaldehyde (cas: 827-01-0Product Details of 827-01-0).

5-Chloroindole-3-carboxaldehyde (cas: 827-01-0) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Product Details of 827-01-0

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles